It’s 2013, you have to act like an equal partner, I get that you’re 16. He may be extremely shy, or he may be broke and can’t afford to take you out and pay for both of you. He also may not be creative enough to even consider what asking you out really means (as in, he may not even know where to take you or what to do when you got there).
Ask him if he’d like to get a cup of coffee, then go dutch. Suggest a picnic, rollerblading in the park, a walk on the beach or a trip to one of your local museums. Insist on going dutch, unless he insists on paying for you. If you do end up dating him on a regular basis, make sure that you both reciprocate with the paying back and forth. Don’t expect him to pay for you all the time.
Learn, now, at your young age, how to be confident, comfortable around, and equal to boys.
If he turns you down (and doesn’t give you a good reason for why he can’t go with you) then stop kissing him and chalk it up to horny hormones in a dude.